There are a large number of oxygen-containing hydrocarbon compounds, including alcohols and esters, which are useful as perfumes. For example, ether alcohols obtained from glycols and alcohols are known as important perfumes. In the prior art production processes, these ether alcohols are produced, for example, by (1) addition reaction of a glycol compound to an olefin compound (U.S. Pat. No. 4,393,247), (2) reduction of an allyl ether hydroformyl compound (U.S. Pat. No. 4,521,634), (3) addition reaction of an alcohol with an epoxide (as disclosed in JP-A-58-159435 (U.S. Pat. No. 4,608,445); the term "JP-A" as used herein means an "unexamined published Japanese patent application") and (4) hydrogenation of an epoxide-added phenol (as disclosed in JP-A-4-217937, (corresponding to U.S. Pat. No. 5,194,423)).
However, these production processes have several problems including low production yield, too many production steps, and the necessity of using hazardous materials such as sodium hydride and the like.
In addition to the above processes, these ether alcohols are also produced by (5) hydrogenolysis of cyclic ketals or cyclic acetals prepared from ketones, aldehydes and the like. Examples of such a process include: a process in which a cyclic ketal is subjected to reduction in the presence of lithium aluminum hydride and aluminum chloride (as disclosed in Organic Synthesis Collective, vol.5, p.303); a process in which a cyclic ketal is subjected to hydrogenolysis in the presence of a platinum or rhodium as a catalyst (as disclosed in JP-A-54-135714 (corresponding to U.S. Pat. No. 4,088,700)); and a process in which a cyclic acetal is subjected to hydrogenolysis in the presence of palladium and phosphoric acid catalysts (as disclosed in JP-A-58-189129 (corresponding to U.S. Pat. No. 4,484,009)), cobalt carbonyl catalyst (as disclosed in Can. J. Chem., vol.54, p.685 (1976)), palladium, platinum or the like catalyst (as disclosed in J.C.S. Chem. Commun., 106 (1981)) or palladium catalyst (as disclosed in JP-B-1-36450 (corresponding to U.S. Pat. No. 4,479,017); the term "JP-B" as used herein means an "examined Japanese patent publication").
However, of these processes for the hydrogenolysis of cyclic ketals and cyclic acetals, the process in which lithium aluminum hydride is used has a problem from an industrial production point of view because the reagent is expensive and hazardous, while the process in which a cyclic ketal is subjected to hydrogenolysis in the presence of platinum or rhodium catalyst (as disclosed in JP-A-54-135714) can produce the ether alcohol only with a low yield. On the other hand, the processes for the catalytic hydrogenolysis of cyclic acetals are reported to be effective in producing ether alcohols with a high yield (as disclosed in JP-A-58-189129 and JP-B-1-36450), but with disadvantages in that in order to obtain a high yield it is necessary to use a large quantity of a diol as a solvent, which serves as the raw material of the acetal, and the yield greatly decreases when the reaction is carried out with a reduced amount of the diol or without the solvent (as disclosed in comparative examples in JP-A-58-189129 and the like).
Accordingly, it is an object of the present invention to provide an industrially advantageous process for the production of ether alcohols, which does not necessarily require a diol solvent and is inexpensive and highly efficient.